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Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides

Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides
Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides
Solid-phase syntheses of novel receptors featuring a 2,6- diamidopyridine "head" group and bearing sulfonamidopeptide sidearms are described, NMR conformational studies show that the 'two-armed" receptors collapse into an intramolecularly folded structure through formation of a hydrogen-bonding network. In order to accommodate the guests, receptors have to unfold, breaking the intramolecular hydrogen bonds. The absolute binding constants of receptors with N-protected amino acids and dipeptides are therefore relatively weak. However, one receptor shows a high selectivity for N-CbZ-D-Ala-D-AlaOH over its enantiomer N-Cbz-L-Ala-L-AlaOH.
enantioselectivity, host-guest systems, molecular recognition, peptides, receptors, selective peptide binding, combinatorial libraries, molecular tweezers, sequence, identification, stabilization, recognition, terminus, water, host
1434-193X
4625-4634
Botana, Enrique
819b6a18-dbc0-41b6-9432-39b02296468b
Ongeri, Sandrine
a53195f8-57af-415a-8cf1-981cd92480b6
Arienzo, Rosa
dd4ed72b-cbdd-4d8e-bc3c-a025f21cf9d6
Demarcus, Mariangela
e2840343-34b4-4446-89ef-0dac6a1cfb7d
Frey, Jeremy G.
ba60c559-c4af-44f1-87e6-ce69819bf23f
Piarulli, Umberto
8b3bd0d3-e506-4e79-9968-588844de4edc
Potenza, Donatella
d5238dbc-98e9-4ead-b7cd-b387ad8d98fd
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Gennari, Cesare
d241412e-a09c-40c0-8f50-7a23f0992131
Botana, Enrique
819b6a18-dbc0-41b6-9432-39b02296468b
Ongeri, Sandrine
a53195f8-57af-415a-8cf1-981cd92480b6
Arienzo, Rosa
dd4ed72b-cbdd-4d8e-bc3c-a025f21cf9d6
Demarcus, Mariangela
e2840343-34b4-4446-89ef-0dac6a1cfb7d
Frey, Jeremy G.
ba60c559-c4af-44f1-87e6-ce69819bf23f
Piarulli, Umberto
8b3bd0d3-e506-4e79-9968-588844de4edc
Potenza, Donatella
d5238dbc-98e9-4ead-b7cd-b387ad8d98fd
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Gennari, Cesare
d241412e-a09c-40c0-8f50-7a23f0992131

Botana, Enrique, Ongeri, Sandrine, Arienzo, Rosa, Demarcus, Mariangela, Frey, Jeremy G., Piarulli, Umberto, Potenza, Donatella, Kilburn, Jeremy D. and Gennari, Cesare (2001) Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides. European Journal of Organic Chemistry, (24), 4625-4634. (doi:10.1002/1099-0690(200112)2001:24<4625::AID-EJOC4625>3.0.CO;2-L).

Record type: Article

Abstract

Solid-phase syntheses of novel receptors featuring a 2,6- diamidopyridine "head" group and bearing sulfonamidopeptide sidearms are described, NMR conformational studies show that the 'two-armed" receptors collapse into an intramolecularly folded structure through formation of a hydrogen-bonding network. In order to accommodate the guests, receptors have to unfold, breaking the intramolecular hydrogen bonds. The absolute binding constants of receptors with N-protected amino acids and dipeptides are therefore relatively weak. However, one receptor shows a high selectivity for N-CbZ-D-Ala-D-AlaOH over its enantiomer N-Cbz-L-Ala-L-AlaOH.

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More information

Published date: 2001
Keywords: enantioselectivity, host-guest systems, molecular recognition, peptides, receptors, selective peptide binding, combinatorial libraries, molecular tweezers, sequence, identification, stabilization, recognition, terminus, water, host

Identifiers

Local EPrints ID: 19422
URI: http://eprints.soton.ac.uk/id/eprint/19422
ISSN: 1434-193X
PURE UUID: 18438bbe-c916-4433-b69f-6ee0960b114d
ORCID for Jeremy G. Frey: ORCID iD orcid.org/0000-0003-0842-4302

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 20 Jul 2019 01:28

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Contributors

Author: Enrique Botana
Author: Sandrine Ongeri
Author: Rosa Arienzo
Author: Mariangela Demarcus
Author: Jeremy G. Frey ORCID iD
Author: Umberto Piarulli
Author: Donatella Potenza
Author: Jeremy D. Kilburn
Author: Cesare Gennari

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